JEE Main · 2019 · Shift-ImediumHC-059

The major product of the following reaction is:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

The major product of the following reaction is: image

Options
  1. a

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  2. b

    image

  3. c

    image

  4. d

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Correct Answera

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Detailed Solution

Step 1: Identify the starting material

The starting material is 1,2-dihydronaphthalene (tetralin with one double bond in the ring) treated with \ceBr2\ce{Br2} in the presence of ethanol (\ceEtOH\ce{EtOH}).

Step 2: Bromonium ion formation

When \ceBr2\ce{Br2} reacts with the alkene in the presence of an alcohol:

  1. Bromonium ion (\ceBr+\ce{Br^+}) forms on the double bond → cyclic bromonium intermediate
  2. The nucleophile (EtOH, not \ceBr\ce{Br^-}) attacks the bromonium ion
  3. EtOH attacks at the more electrophilic carbon (benzylic position)
  4. Anti addition → trans product

Step 3: Regiochemistry and stereochemistry image

  • EtOH attacks at the benzylic carbon (C1 of the ring system, adjacent to aromatic ring) — more electrophilic due to benzylic stabilization
  • \ceBr\ce{Br-} is incorporated at C2
  • Anti addition → trans configuration of OEt and Br

Product = trans-1-ethoxy-2-bromotetralin (trans-2-bromo-1-ethoxytetralin)

Answer: Option (a)

Key Points to Remember:

  • In ROH solvent, the alcohol acts as the nucleophile (instead of \ceBr\ce{Br-}) → mixed product
  • EtOH attacks the more electrophilic (benzylic) carbon
  • Anti addition → trans relationship between OR and Br
  • This reaction is used to make bromohydrin ethers

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